Water → Methyl 2-(3-amino-4-chlorophenoxy)acetate

HRID 2266505Notes

Reaction equation

HRID 2266505 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([N+:13]([O-])=O)[CH:7]=1.[Cl-].[NH4+].O.[OH-].[Na+]>CO.[Fe]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH2:13])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 66717584(4-chloro-3-nitrophenoxy)acetic Acid Methyl Ester

Product 1

HCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (4-chloro-3-nitrophenoxy)acetic acid methyl ester (30 g) in methanol (100 mL) was added to a mixture of iron (26 g), ammonium chloride (33 g) and water (400 mL) at room temperature. The resulting mixture was heated in an ultrasonic bath at 60° C. for 4 hours. The mixture was basified by the addition of sodium hydroxide and then extracted with ethyl acetate. The combined extracts were washed with 1.0 M aqueous hydrochloric acid and the pH of the combined aqueous phases were adjusted to 7-8 by the addition of sodium hydroxide. The resulting precipitate was collected by filtration and dried to afford title compound, 14 g.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with 1.0 M aqueous hydrochloric acid
  3. additionthe pH of the combined aqueous phases were adjusted to 7-8 by the addition of sodium hydroxide
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-c9982a0088e54c9da0db50b0627a3b3b
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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